Benzyl mercaptan → HCID 53885188, compound

HRID 393117Notes

Reaction equation

HRID 393117 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:19])[CH:13]=[C:14]([CH3:18])[CH2:15][CH2:16][CH3:17])[CH3:10]>N1CCCCC1>[CH2:9]([O:11][C:12](=[O:19])[CH2:13][C:14]([S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:18])[CH2:15][CH2:16][CH3:17])[CH3:10]

Participants

4

Reactant 2

HCID 7509Benzyl mercaptanHCID 53402000HCID 53402000, compound

Product 1

HCID 53885188HCID 53885188, compound

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A mixture of 62.1 g (0.5 mol) of benzyl mercaptan and 78.1 g (0.5 mol) of (rac)-3-methyl-2-hexenoic acid ethyl ester of step (a) in 100 ml of piperidine was heated at reflux until complete reaction was observed (48 h), and cooled to room temperature. Then the excess of piperidine was distilled off at reduced pressure (0.04 mbar, 26-33° C.). The residue, 96.5 g (68%) of (rac)-3-benzylsulfanyl-3-methyl-hexanoic acid ethyl ester, was of good purity and was directly used in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until complete reaction
  3. custom(48 h)
  4. distillationThen the excess of piperidine was distilled off at reduced pressure (0.04 mbar, 26-33° C.)

Sources & evidence

ORD record
ord-2013e43798204b0e802ef0d19e1dc3a6
Source dataset
uspto-grants-2004_10
Patent number
US06805893B2

Reaction notes

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